1,4-Dibromobutane → 1-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile

HRID 7719

反応式

HRID 7719 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[C:12]([Cl:19])[CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:31][CH2:32][CH2:33][CH2:34]Br>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:17]#[N:18])[CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:12]([Cl:19])[CH:11]=1

参加物

5

反応物 3

HCID 80561,4-DibromobutaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10286072[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile

生成物 1

HCID 102865191-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (270 mg, 1.0 mmol) and THF (20 mL) was cooled to −78° C. A solution of NaHMDS (3.7 mL, 2.2 mmol, 0.6M solution in PhMe) was added dropwise via syringe to the reaction. After 15 min at −78° C., 1,4-dibromobutane (143 μL, 1.2 mmol) was added dropwise via syringe. The cooling bath was removed, and the reaction was allowed to warm to rt. The reaction was quenched by the addition of silica gel (600 mg) and concentrated to dryness. The residue was purified by flash chromatography on silica gel (EtOAc:hexanes 1:5) to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.34 (s, 1H), 8.12 (dd, 1H), 7.77–7.80 (m, 1H), 7.56–7.62 (m, 2H), 7.35–7.42 (m, 2H), 2.71–2.78 (m, 2H), 2.14–2.26 (m, 2H), 1.89–2.01 (m, 4H). MS (ESI) 323 (M+H)+.

後処理

  1. customThe cooling bath was removed
  2. customThe reaction was quenched by the addition of silica gel (600 mg)
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash chromatography on silica gel (EtOAc:hexanes 1:5)

出典と根拠

ORDレコード
ord-f11ad2c55b7f49aca6d002758dd0a103
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

読み込み中…